Donald Trump’s presidential campaign is suffused with nostalgia. His slogan is “Make America Great Again,” after all. Many of his supporters yearn for a return to an unspecified era of prosperity and patriotism, before what they see as today’s suffocating political correctness.

But in bringing up the marital infidelities of Hillary Clinton’s husband, as Mr. Trump and his surrogates are doing in the wake of his much-panned performance in Monday’s debate, the GOP nominee may be indulging in a sort of nostalgia that is unlikely to benefit his White House bid. In part that may be because the values of a number American voters are very different than the distant era of 1998.

While such an appeal might resonate among his white, male base, women and Millennial generation voters are particularly unlikely to be moved by Trump’s attempts to link Mrs. Clinton with President Bill Clinton’s affairs and impeachment, says Jennifer Lawless, director of the Women and Politics Institute and a professor of government at American University.

For many women, when Trump talks about the subject of sex, they’ll hear the word “gender.” They’ll interpret Trump’s words as implicit criticism of Clinton’s decisions about her marriage at the time, and as an effort to disparage a wife for the transgressions of the husband.

For Millennials, they’ll hear about Monica Lewinsky and Gennifer Flowers and Ken Starr and tune out. The youngest eligible voters today weren’t even born when news broke that President Clinton was having an affair with a young intern. Litigating old conflicts probably isn’t a great way to sway Millennial votes.

“I don’t think this is going to work like Trump thinks it will,” says Professor Lawless. “It makes me feel like the last 20 years didn’t happen.”

On one hand, it’s a clear way of highlighting the old scandals (or perceived scandals) of the Clinton years. It suggests to voters they can expect the same again if they elect a second Clinton to office. And it might work for those who lived through that period and disliked it.

But many of today’s voters – women in particular – may also think it suggests something more offensive, says Lawless: that Hillary Clinton was not sufficient as a wife, and this made Mr. Clinton stray.

“It’s a suggestion to voters that maybe they need to look elsewhere like Bill did,” says Lawless.

Dropping hints

For his part, Trump is treating references to Mr. Clinton’s infidelities as explosive material.

In an oblique reference at the end of Monday’s debate Trump said that he had been going to say something “extremely rough” to Clinton but had refrained because it was “inappropriate.” Since then has dropped a few direct references. On Thursday at a campaign rally in New Hampshire, at one point Trump said, “An impeachment for lying,” referring to the attempt to remove Mr. Clinton from office for lying about his affair with Ms. Lewinsky. “Remember that? Impeach.”

The Trump campaign has told surrogates to raise the issue more directly. If asked about the ongoing dispute over Alicia Machado, the former Miss Universe whom Trump continues to disparage for having gained weight during her reign as pageant winner, surrogates should pivot to the Lewinsky scandal, according to the Trump campaign.

They should say Mrs. Clinton “bullied and smeared” women who have accused Mr. Clinton of sexual harassment, according to Trump campaign talking points obtained by NBC News.

In the past, Clinton has indeed lashed out at women who have charged her husband with misconduct. In the early 1990s, she dismissed Ms. Flowers’ statement of an affair with Mr. Clinton. Flowers was “some failed cabaret singer,” Mrs. Clinton said at the time.

In 1998, Mr. Clinton acknowledged having sexual contact with Flowers.

However, the political problem for Trump is that in 1998, the voters generally saw impeachment as being largely about sex, not lying. Nor did they punish Mrs. Clinton for defending her husband. Her favorability rating rose from 64 to 66 percent in polls, at that time a personal best.

How it plays today

Today, initial indicators are that the issue might be particularly toxic with crucial female swing voters. Anti-Trump GOP strategists Tim Miller and Katie Packer told NBC that they conducted focus groups on the subject before the Republican primaries, and concluded that “voters were completely turned off and disgusted by it.”

Perhaps more telling is that many Trump supporters are publicly saying that the GOP nominee should refrain from raising this subject.

“It’s totally the wrong direction to go,” said Trump backer and former House Speaker Newt Gingrich, who pushed for Mr. Clinton’s impeachment, on Thursday.

So what’s Trump up to? It’s possible that this attack is aimed at the one section of voters sure to find it attractive, Trump’s base, says Brian Rosenwald, a political historian at the University of Pennsylvania and author of a forthcoming book on the political impact of talk radio. It could be meant to evoke not just the memory of impeachment but also the entire swirl of Clinton drama. That’s an era many Republicans do not remember fondly.

“It reminds them of what they hate about the Clintons,” says Professor Rosenwald.

Or Trump might think this could appeal to younger voters who are already anti-Clinton inclined. They could view the Lewinsky-Clinton encounter as an encounter that reflected a power imbalance between an older man and a younger woman. They could see Clinton’s harsh words about her husband’s accusers as victim-shaming. That might be more in keeping with the cultural values and experience of many Millennials.

But that assumes that the veer toward talking about scandal was premeditated. That might not be the case. It’s possible that Trump, himself thrice-married and someone who had an affair that ended his first marriage, is just angry about the debate and responding in an emotional way.

“The right candidate could probably bring it up and benefit, at least on the margins. But Trump isn’t that candidate,” says Rosenwald.